AU3812689A - Derivatives of n-phenylpyrazoles - Google Patents

Derivatives of n-phenylpyrazoles

Info

Publication number
AU3812689A
AU3812689A AU38126/89A AU3812689A AU3812689A AU 3812689 A AU3812689 A AU 3812689A AU 38126/89 A AU38126/89 A AU 38126/89A AU 3812689 A AU3812689 A AU 3812689A AU 3812689 A AU3812689 A AU 3812689A
Authority
AU
Australia
Prior art keywords
substituted
triazol
bromine
iodine
chlorine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
AU38126/89A
Other versions
AU623157B2 (en
Inventor
Ian George Buntain
Leslie Roy Hatton
David William Hawkins
Christopher John Pearson
David Alan Roberts
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Agriculture Ltd
Original Assignee
May and Baker Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by May and Baker Ltd filed Critical May and Baker Ltd
Publication of AU3812689A publication Critical patent/AU3812689A/en
Application granted granted Critical
Publication of AU623157B2 publication Critical patent/AU623157B2/en
Assigned to RHONE-POULENC AGRICULTURE LIMITED reassignment RHONE-POULENC AGRICULTURE LIMITED Alteration of Name(s) in Register under S187 Assignors: MAY & BAKER LIMITED
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

An N-phenylpyrazole derivative of the formula: <CHEM> wherein R<1> represents cyano, nitro or halogen; R<2> represents a group R<5>SO2, R<5>SO, or R<5>S in which R<5> represents alkyl, alkenyl or alkynyl unsubstituted or substituted by halogen; R<3> represents azido or hydrazino, or pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,4-triazol-4-yl, 1,2,4-triazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, piperidino, pyrrolidino, morpholino or N-alkylpiperazino, which may be substituted by alkyl or phenyl; and R<4> represents phenyl substituted in the 2-position by fluorine, chlorine, bromine or iodine; in the 4-position by alkyl or alkoxy unsubstituted or substituted by halogen, or fluorine, chlorine, bromine or iodine; and unsubstituted or substituted in the 6-position by fluorine, chlorine, bromine or iodine and pesticidally acceptable acid addition salts thereof possess arthropodicidal, nematocidal, anthelmintic and anti-protozoal activity.
AU38126/89A 1988-07-15 1989-07-14 Derivatives of n-phenylpyrazoles Ceased AU623157B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB888816915A GB8816915D0 (en) 1988-07-15 1988-07-15 New compositions of matter
GB8816915 1988-07-15

Publications (2)

Publication Number Publication Date
AU3812689A true AU3812689A (en) 1990-01-18
AU623157B2 AU623157B2 (en) 1992-05-07

Family

ID=10640538

Family Applications (1)

Application Number Title Priority Date Filing Date
AU38126/89A Ceased AU623157B2 (en) 1988-07-15 1989-07-14 Derivatives of n-phenylpyrazoles

Country Status (25)

Country Link
US (1) US4963575A (en)
EP (1) EP0352944B1 (en)
JP (1) JP2870650B2 (en)
AT (1) ATE119158T1 (en)
AU (1) AU623157B2 (en)
CA (1) CA1337766C (en)
CZ (1) CZ283116B6 (en)
DE (1) DE68921384T2 (en)
DK (1) DK350289A (en)
ES (1) ES2068895T3 (en)
FI (1) FI102278B (en)
GB (1) GB8816915D0 (en)
GR (1) GR3015242T3 (en)
HU (1) HUT51456A (en)
IE (1) IE67069B1 (en)
IL (1) IL90967A0 (en)
MA (1) MA22037A1 (en)
MY (1) MY106975A (en)
NO (1) NO892885L (en)
NZ (1) NZ229936A (en)
OA (1) OA10556A (en)
PH (1) PH26899A (en)
PT (1) PT91176B (en)
TR (1) TR24437A (en)
ZA (1) ZA895389B (en)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
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US5187185A (en) * 1988-12-09 1993-02-16 Rhone-Poulenc Ag Company Pesticidal 1-arylpyrroles
GB8920521D0 (en) * 1989-09-11 1989-10-25 May & Baker Ltd New compositions of matter
EP0508527A1 (en) * 1991-04-11 1992-10-14 UNIROYAL CHEMICAL COMPANY, Inc. New fungicidally active pyrazole compounds
DE4343832A1 (en) 1993-12-22 1995-06-29 Bayer Ag Substituted 1-arylpyrazoles
US5629335A (en) * 1995-04-07 1997-05-13 Rhone-Poulenc Inc. Pesticidal 1-arylpyrazole-3-carboximidothioic acid esters
US6136983A (en) * 1995-06-05 2000-10-24 Rhone-Poulenc Agrochimie Pesticidal sulfur compounds
US6060502A (en) * 1995-06-05 2000-05-09 Rhone-Poulenc Agrochimie Pesticidal sulfur compounds
US6060495A (en) * 1995-06-05 2000-05-09 Rhone-Poulenc Agrochimie Pesticidal sulfur compounds
FR2752525B1 (en) * 1996-08-20 2000-05-05 Rhone Merieux METHOD FOR CONTROLLING MYIA OF CATTLE AND SHEEP HERBS AND COMPOSITIONS FOR CARRYING OUT SAID METHOD
US6413542B1 (en) 1996-03-29 2002-07-02 Merial Direct pour-on antiparasitic skin solution and methods for treating, preventing and controlling myasis
IE80657B1 (en) 1996-03-29 1998-11-04 Merial Sas Insecticidal combination to control mammal fleas in particular fleas on cats and dogs
FR2750861B1 (en) * 1996-07-11 1998-12-24 Rhone Merieux PROCESSES FOR REMOVING PARASITES, ESPECIALLY VERTEBRATE ECTOPARASITES, ESPECIALLY MAMMALS AND COMPOSITIONS FOR CARRYING OUT THIS PROCESS
EP0915655B9 (en) * 1996-07-23 2005-09-07 Merial Process and composition for the antiparasitic treatment of the surroundings of animals
US6998131B2 (en) * 1996-09-19 2006-02-14 Merial Limited Spot-on formulations for combating parasites
US6426333B1 (en) 1996-09-19 2002-07-30 Merial Spot-on formulations for combating parasites
DE19650197A1 (en) 1996-12-04 1998-06-10 Bayer Ag 3-thiocarbamoylpyrazole derivatives
US6350771B1 (en) 1996-12-24 2002-02-26 Rhone-Poulenc, Inc. Pesticidal 1-arylpyrazoles
ZA9711534B (en) 1996-12-24 1998-06-24 Rhone Poulenc Agrochimie Pesticidal 1-arylpyrazoles.
CO5060426A1 (en) * 1997-03-10 2001-07-30 Rhone Poulenc Agrochimie 1-ARIL-3-PESTICIDE IMIDIOPIRAZOLES
ZA981776B (en) 1997-03-10 1998-09-03 Rhone Poulenc Agrochimie Pesticidal 1-arylpyrazoles
US5981565A (en) 1997-10-07 1999-11-09 Rhone-Poulenc Inc. Pyrazole pesticides
US6107314A (en) * 1997-10-07 2000-08-22 Rhone-Poulenc Inc. Pesticides
EP0911329A1 (en) * 1997-10-07 1999-04-28 Rhone-Poulenc Agro 3-Substituted arylpyrazole derivatives
CO5221057A1 (en) 2000-03-02 2002-11-28 Aventis Cropscience Sa PESTICIATED COMPONENTS AND COMPOSITIONS
US7262214B2 (en) 2003-02-26 2007-08-28 Merial Limited 1-N-arylpyrazole derivatives in prevention of arthropod-borne and mosquito-borne diseases
US7531186B2 (en) 2003-12-17 2009-05-12 Merial Limited Topical formulations comprising 1-N-arylpyrazole derivatives and amitraz
US20050234119A1 (en) * 2004-04-16 2005-10-20 Soll Mark D Antiparasitical agents and methods for treating, preventing and controlling external parasites in animals
US20070232586A1 (en) * 2004-04-21 2007-10-04 Kazuyuki Ohmoto Hydrazino-Substituted Heterocyclic Nitrile Compounds and Use Thereof
US20060046988A1 (en) 2004-08-30 2006-03-02 Albert Boeckh Methoprene formulations for the control of tick infestations
CN101175729B (en) * 2004-12-07 2011-06-01 梅瑞尔有限公司 1-phenyl-3-piperazine-pyrazoles and pesticidal compositions of matter thereof
HUE027891T2 (en) 2006-07-05 2016-11-28 Merial Inc 1-Aryl-5-alkyl pyrazole derivative compounds, processes of making and methods of using thereof
FR2925337B1 (en) * 2007-12-21 2010-01-15 Virbac PHARMACEUTICAL COMPOSITION CONTAINING AN N-PHENYLPYRAZOLE DERIVATIVE AND GLYCOFUROL, USE FOR THE PREPARATION OF A TOPICAL VETERINARY DRUG FOR CONTROLLING CHIPS
US9173728B2 (en) 2008-11-19 2015-11-03 Merial Inc. Multi-cavity container having offset indentures for dispensing fluids
AU2009316899B2 (en) 2008-11-19 2015-08-20 Boehringer Ingelheim Animal Health USA Inc. Compositions comprising 1-arylpyrazole alone or in combination with formamidine for the treatment of parasitic infection
WO2010070210A1 (en) 2008-12-16 2010-06-24 Virbac Pharmaceutical composition containing an n-phenylpyrazole derivative, and use thereof for preparing a topical veterinary drug for flea control
AU2010224685A1 (en) 2009-03-18 2011-11-03 Fidopharm, Inc. Parasiticidal formulation
NZ597929A (en) 2009-07-30 2013-09-27 Merial Ltd Insecticidal 4-amino-thieno[2,3-d]-pyrimidine compounds and methods of their use
CA2784141C (en) 2009-12-17 2017-10-24 Merial Limited Compositions comprising macrocyclic lactone compounds and spirodioxepinoindoles
UA108641C2 (en) 2010-04-02 2015-05-25 PARASITICID COMPOSITION CONTAINING FOUR ACTIVE AGENTS AND METHOD OF APPLICATION
WO2012107585A1 (en) 2011-02-11 2012-08-16 Ceva Sante Animale Sa Novel concentrated and stable topical antiparasitic compositions
US9925167B2 (en) 2011-06-30 2018-03-27 Hansen-Ab Gmbh Agents for the control of parasites on animals
US9173404B2 (en) 2011-11-17 2015-11-03 Merial, Inc. Compositions comprising an aryl pyrazole and a substituted imidazole, methods and uses thereof
JO3626B1 (en) 2012-02-23 2020-08-27 Merial Inc Topical compositions comprising fipronil and permethrin and methods of use
TWI579274B (en) 2012-04-20 2017-04-21 龍馬躍公司 Improved processes for the preparation of 1-aryl-5-alkyl pyrazole compounds
CN102675205B (en) * 2012-05-25 2014-08-20 安徽农业大学 Pyrazol oxime ether compound and preparation method and application thereof in anticancer therapy
FR3000393B1 (en) 2012-12-27 2015-01-16 Virbac TOPICAL ASSOCIATION OF N-PHENYLPYRAZOLE AND PERMETHRIN
ES2887302T3 (en) 2014-10-31 2021-12-22 Boehringer Ingelheim Animal Health Usa Inc Parasiticidal compositions comprising fipronil
US9392792B1 (en) 2014-12-30 2016-07-19 Virbac Topical combination of fipronil, permethrin and pyriproxyfen
CN105541821B (en) * 2016-01-28 2018-05-18 中南民族大学 Oxazine assimilation arylpyrazole type compound and its Ultrasonic Radiation synthetic method and application
CN110256351B (en) * 2019-06-13 2024-03-15 北京大学 Synthesis method of fipronil and analogue thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3528478A1 (en) * 1985-08-08 1987-02-12 Bayer Ag 1-ARYL-5-HYDRAZINO-PYRAZOLE
DE3528477A1 (en) * 1985-08-08 1987-02-19 Bayer Ag 1-ARYL-PYRAZOLE
DE3545036A1 (en) * 1985-12-19 1987-09-10 Bayer Ag 5-HETEROCYCLYL-1-ARYL-PYRAZOLE
DE3545347A1 (en) * 1985-12-20 1987-07-02 Bayer Ag 1-ARYL-PYRAZOLE
GB8713768D0 (en) * 1987-06-12 1987-07-15 May & Baker Ltd Compositions of matter
GB8531485D0 (en) * 1985-12-20 1986-02-05 May & Baker Ltd Compositions of matter
DE3616681A1 (en) * 1986-05-16 1987-11-19 Bayer Ag 1-ARALKYLPYRAZOLE

Also Published As

Publication number Publication date
FI102278B1 (en) 1998-11-13
ZA895389B (en) 1990-04-25
FI893443A (en) 1990-01-16
NO892885L (en) 1990-01-16
CZ283116B6 (en) 1998-01-14
JP2870650B2 (en) 1999-03-17
ES2068895T3 (en) 1995-05-01
JPH0269464A (en) 1990-03-08
FI893443A0 (en) 1989-07-14
NO892885D0 (en) 1989-07-13
IL90967A0 (en) 1990-02-09
DK350289D0 (en) 1989-07-14
GR3015242T3 (en) 1995-06-30
FI102278B (en) 1998-11-13
PH26899A (en) 1992-12-03
IE892291L (en) 1990-01-15
MA22037A1 (en) 1991-10-01
PT91176B (en) 1995-03-01
DK350289A (en) 1990-01-16
DE68921384T2 (en) 1995-06-29
IE67069B1 (en) 1996-02-21
PT91176A (en) 1990-02-08
AU623157B2 (en) 1992-05-07
ATE119158T1 (en) 1995-03-15
US4963575A (en) 1990-10-16
CA1337766C (en) 1995-12-19
EP0352944A1 (en) 1990-01-31
NZ229936A (en) 1990-09-26
OA10556A (en) 2002-05-06
EP0352944B1 (en) 1995-03-01
DE68921384D1 (en) 1995-04-06
HUT51456A (en) 1990-05-28
GB8816915D0 (en) 1988-08-17
CZ431589A3 (en) 1997-08-13
TR24437A (en) 1991-10-09
MY106975A (en) 1995-08-30

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